1,2,4‐Oxadiazole‐Bridged Polynitropyrazole Energetic Materials with Enhanced Thermal Stability and Low Sensitivity
A family of mono or di(1,2,4‐oxadiazole)‐bridged polynitropyrazole derivatives with C‐nitro/N‐nitro functionalities is reported. All compounds were fully characterized by IR, NMR (1H, 13C), elemental analysis and differential scanning calorimetry (DSC). The solid‐state structure features were further investigated with X‐ray diffraction. Of these, compounds 3,5‐bis(3,4‐dinitro‐1H‐pyrazol‐5‐yl)‐1,2,4‐oxadiazole (3 a) and 5,5′‐bis(3,4‐dinitro‐1H‐pyrazol‐5‐yl)‐3,3′‐bi(1,2,4‐oxadiazole) (3 b) possess high thermal stability (3 a: Tdec=274 °C; 3 b: Tdec=272 °C), sensitivity (IS >30 J, FS >360 N) and comparable detonation properties (3 a: Dv=8741 m s−1, P=34.0 GPa; 3 b: Dv=8685 m s−1, P=33.4 Gpa) to RDX. In addition, 3,5‐bis(4‐nitro‐1H‐pyrazol‐3‐yl)‐1,2,4‐oxadiazole (4 a) and 5,5′‐bis(4‐nitro‐1H‐pyrazol‐3‐yl)‐3,3′‐bi(1,2,4‐oxadiazole) (4 b) have high decomposition temperature (4 a: Tdec=314 °C; 4 b: Tdec=317 °C), low sensitivity (IS >40 J; FS>360 N) and superior detonation performances (4 a: Dv=8027 m s−1, P=26.4 GPa; 4 b: Dv=7991 m s−1, P=25.2 Gpa) than conventional heat‐resistant explosive hexanitrostilbene (HNS: Tdec=318 °C; IS=5 J; FS=240 N; Dv=7612 m s−1, P=24.3 GPa), thus suggesting their potential application as heat‐resistant explosives.
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